WO2000009506A1 - Derives de 1h-imidazopyridine - Google Patents
Derives de 1h-imidazopyridine Download PDFInfo
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- WO2000009506A1 WO2000009506A1 PCT/JP1999/004381 JP9904381W WO0009506A1 WO 2000009506 A1 WO2000009506 A1 WO 2000009506A1 JP 9904381 W JP9904381 W JP 9904381W WO 0009506 A1 WO0009506 A1 WO 0009506A1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Definitions
- the present invention has a potent inhibitory effect on the production of tumor necrosis factor (TNF) and interleukin-1 (IL-1) and is a chronic inflammatory disease in humans or animals (eg, rheumatoid arthritis, osteoarthritis, etc.) , Allergic rhinitis, atopic dermatitis, contact dermatitis, asthma, sepsis, septic shock, various autoimmune diseases [autoimmune blood disease (eg, hemolytic anemia, aplastic anemia, idiopathic thrombocytopenia) Disease), autoimmune bowel disease (eg, ulcerative colitis, Crohn's disease), autoimmune keratitis (eg, keratoconjunctivitis sicca, spring conjunctivitis, etc.), endocrine ocular disorders, Graves' disease, sarcoidosis, Multiple sclerosis, systemic lupus erythematosus, polychondritis, scleroderma, active chronic he
- imiquimod has several cytokine-inducing effects, such as interferon (IFN), TNF, and IL-11, as reported in the Journal of Interferon Research. ), Vol. 14, p. 81 (1994), but 1H-imidazopyridine derivatives and 1H having an inhibitory effect on the production of TNF and IL-1 which are completely inconsistent with these prior arts. —I Midazoquinoline derivatives have never been known before. Disclosure of the invention
- An object of the present invention is to provide a novel compound which has an excellent inhibitory effect on the production of cytokines such as TNFIIL-l and is useful as a medicament.
- the present inventors have conducted intensive studies to solve such problems, and as a result, have found a novel 1 H-imidazopyridine derivative having an excellent TNF and IL-11 production inhibitory action, and completed the present invention.
- R 1 represents a hydrogen atom, a hydroxyl group, an alkyl group which may have one or more substituents, a cycloalkyl group which may have a substituent
- R 2 may have a hydrogen atom, an alkyl group, a halogen atom, a hydroxyl group, and one or two substituents
- a ⁇ represents one or more alkyl groups or alkoxy groups
- R 3 represents a saturated nitrogen-containing heterocyclic group which may have a substituent
- m represents an integer of 0 to 3.
- R 3 represents an unsubstituted piperidin
- the present invention relates to a novel 1H-imidazopyridine derivative represented by or a salt thereof.
- R 4 is a hydrogen atom, an alkyl group, a benzyl group, a triphenylmethyl group, an alkanoyl group which may have a substituent, an alkoxycarbonyl A benzyloxycarbonyl group, a thiocarbamoyl group which may have a substituent, an alkanesulfonyl group, a benzenesulfonyl group or an amidino group which may have a substituent, and Y is a methylene group, an oxygen atom , A sulfur atom, a nitrogen atom, a group or a bond represented by NH, and n represents an integer of 0 to 2.)
- a medicament comprising, as an active ingredient, the compound represented by the general formulas (I) and (II) or a pharmaceutically acceptable salt thereof.
- This medicine is used for the treatment of chronic inflammatory diseases (eg, rheumatoid arthritis, osteoarthritis, etc.) in mammals including humans, allergic rhinitis, atopic dermatitis, contact dermatitis, asthma, Sepsis, septic shock, various autoimmune diseases [autoimmune blood diseases (eg, hemolytic anemia, aplastic anemia, idiopathic thrombocytopenia, etc.), autoimmune bowel diseases (eg, ulcerative colitis, Crohn's disease, etc.), autoimmune keratitis (eg, keratoconjunctivitis sicca, spring conjunctivitis, etc.), endocrine ocular disorders, Graves' disease, sarcoidosis, multiple sclerosis, systemic lupus erythematosus, polychondriti
- cytokine-mediated diseases such as TNF or IL-1.
- a tumor necrosis factor (TNF) production inhibitor or an inulin leukin-11 comprising as an active ingredient the compound represented by the general formulas (I) and (II) or a pharmacologically acceptable salt thereof.
- TNF tumor necrosis factor
- IL-1 production inhibitors are provided by the present invention.
- the compound represented by the general formula (II) is a compound represented by the general formula (I) it is characterized by having a specific particular which may have a substituent saturated nitrogen-containing heterocyclic group as R 3.
- the scope of the present invention is not limited to the compound represented by the general formula (II), and any of the compounds having a saturated nitrogen-containing heterocyclic group which may have a substituent as R 3 includes: It goes without saying that it is included in the scope of the present invention.
- R " the alkyl group represented by R 2 and R 4, for example, a methyl group, Echiru group, .eta. propyl group, an isopropyl group, n- Examples include butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.
- Examples of the cycloalkyl group represented by R 1 include a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cycloheptyl group.
- Examples of the aryl group represented by R 1 include: Phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, pyrazinyl, 2- Furyl, 3-furyl, 2-phenyl, 3-phenyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl , 1-Bilazolyl group, 3-Bilazolyl group, 4-Pyrazolyl group, 5-Pyrazolyl group, 2-Oxazolyl group, 4-Oxazolyl
- Examples of the halogen atom represented by R 2 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and an amino group which may have one or two substituents represented by R 2 Examples thereof include an amino group, a methylamino group, an ethylamino group, an n-propylamino group, an isopropylamino group, a cyclopropylamino group, a cyclobutylamino group, a cyclopentylamino group, a cyclohexylamino group, and a dimethylamino group.
- a cyclic amino group represented by R 2 includes, for example, a benzyl group, a acetylamino group, a phenylamino group, a pyridylamino group, a 4-pyridylmethylamino group, a benzylamino group, a p-methoxybenzylamino group, and a dibenzylamino group.
- examples of the homo or hetero ring represented by the ring A include, for example, a benzene ring, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, a cyclooctene ring, and a cycloheptadiene.
- Is for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isoptyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n -Hexyl group and the like
- the alkoxy group which may be substituted includes, for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, ⁇ -pentyloxy, isopentyloxy, neopentyloxy, n-hexyloxy, etc.
- Good halogen atoms include, for example, fluorine, chlorine, bromine and iodine. The number and type of these substituents are not particularly limited, and when two or more substituents are present, they may be the same or different.
- the saturated nitrogen-containing heterocyclic group represented by R 3 has at least one nitrogen atom as a ring-constituting atom, and further has an oxygen atom or a sulfur atom as a ring-constituting atom.
- -Piperidyl group 4-piperidyl group, 1-piperazinyl A 2-piperazinyl group, a 3-pyrrolidinyl group, a 2-azetidinyl group, a 3-azetidinyl group, a 2-morpholinyl group, and a 2-thiomorpholinyl group.
- examples of the alkanol group which may have a substituent represented by R 4 include, for example, formyl group, acetyl group, propionyl group, n-butyryl group, isoptyryl group, valeryl group, isovaleryl Group, bivaloyl group, fluoroacetyl group, difluoroacetyl group, trifluoroacetyl group, chloroacetyl group, dichloroacetyl group, trichloroacetyl group, and the like.
- the alkoxycarbonyl group represented by R 4 includes For example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentylo Xycarbonyl group, n-hexyloxycarbonyl And thiocarbamoyl which may have a substituent represented by R 4 include, for example, thiocarbamoyl, methylthiocarbamoyl, ethylthiocarbamoyl, n-propylthiocarbamoyl, isopropylthio Alkamosulfonyl group, n-butylthio alkamoyl group, isobutylthio sorbamoyl group, sec-butylthio sorbamoyl group, tert-but
- alkane sulfonyl group represented by R 4 examples include methanesulfonyl Ki, Eta And sulfonyl group, n-propanesulfonyl group, n-butanesulfonyl group and the like.
- the substitution / bonding site of the “aryl group”, the “homologous or heterocyclic group” and the “saturated nitrogen-containing heterocyclic group” is, as partially exemplified above, particularly the substitution / bonding site.
- the term is used as a concept including a group which may be substituted / bonded at any position in the ring constituent as long as it is an element which can be substituted / bonded.
- any functional group may be used as long as it is a group capable of substituting these groups.
- the number and types of the substituents are not particularly limited. When two or more substituents are present, they may be the same or different.
- halogen atoms such as a fluorine atom, a chlorine atom, and a bromine atom, a hydroxyl group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, Alkyl groups such as n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, aryl groups such as trifluoromethyl group, phenyl group, naphthyl group, pyridyl group, methoxy group, ethoxy group , N-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, alkoxy group such as tert-butoxy group, aryloxy group such as phenoxy group, amino group,
- Alkylthiol group Lumbamoyl group, amidino group, methylthio group, etc.
- alkylthio group methanesulfinyl group Alkanesulfonyl, methanesulfonyl, benzenesulfonyl, n-propanesulfonyl, n-butanesulfonyl, and other alkanesulfonyl, p-toluenesulfonyl, p-methoxybenzenesulfonyl, p-fluoro Arylsulfonyl groups such as benzenesulfonyl group, aralkyl groups such as benzyl group, naphthyl group, pyridylmethyl group, furfuryl group, triphenylmethyl group, nitro group, cyano group, sulfamoyl group, oxo group, hydroxy group Imino group, methoxymino And ethoxyimino groups, alkoxyimino groups such as n-propoxyimino group, and
- the compounds represented by the above general formulas (I) and (II) of the present invention can be converted into a salt, preferably a pharmacologically acceptable salt, or a base can be liberated from the produced salt, if desired. You can also.
- the salts of the compounds of the present invention represented by the general formulas (I) and (II), preferably pharmaceutically acceptable salts, include acid addition salts, for example, hydrochloric acid, hydrobromic acid, iodine Mineral acid salts such as hydrofluoric acid, nitric acid, sulfuric acid and phosphoric acid, or acetic acid, propionic acid, butyric acid, formic acid, valeric acid, maleic acid, fumaric acid, citric acid, oxalic acid, malic acid, Succinic acid, lactic acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, mandelic acid, 10-camphorsulfonic acid, tartaric acid, stearic acid, gluconic acid, nicotinic acid, trifluoroacetic acid, benzoic acid, etc.
- Organic acid salts for example, hydrochloric acid,
- compounds having an asymmetric carbon may have optical isomers, and the present invention also includes these optically active isomers and mixtures thereof. Included.
- the compound represented by the above general formulas (I) and (II) or a salt thereof according to the present invention can exist in any crystal form depending on the production conditions, and exist as an arbitrary hydrate or solvate. However, these crystal forms, hydrates or solvates, and mixtures thereof are also included in the scope of the present invention.
- Preferred compounds of the present invention include, for example, the following compounds and salts thereof, but the present invention is not limited to these examples.
- the novel 1 H-imidazopyridin derivative represented by the general formula (I) or ( ⁇ ) of the present invention can be produced by various methods, but the method of producing the compound of the present invention is not limited to these methods. It is not done. In the following production methods, the compound represented by the general formula (I) will be specifically described. However, it is noted that the compound represented by the general formula ( ⁇ ) is included in these production methods. It is obvious.
- the following synthesis method is used according to the method disclosed in JP-A-3-206078 or Tetrahedron, Vol. 51, p. 5813 (1995). be able to.
- R 5 represents a hydroxyl group or an alkyl group
- R 6 represents a chlorine atom or an alkyl group
- R represents the same meaning as R 1 (excluding the hydroxyl group)
- the compound represented by the general formula (III) is treated with a nitric acid such as concentrated nitric acid or fuming nitric acid in the presence or absence of acetic acid or sulfuric acid at 0 ° C to 200 ° C.
- a nitric acid such as concentrated nitric acid or fuming nitric acid
- acetic acid or sulfuric acid at 0 ° C to 200 ° C.
- step 2 the compound of the general formula (IV) is treated with a suitable chlorinating agent, for example, oxyphosphorus chloride, thionyl chloride, phosgene, oxalyl chloride, phosphorus pentachloride, etc., in the presence or absence of a solvent such as toluene.
- a suitable chlorinating agent for example, oxyphosphorus chloride, thionyl chloride, phosgene, oxalyl chloride, phosphorus pentachloride, etc.
- step 3 the amine represented by the general formula (VI) and the compound represented by the general formula (V) are mixed with a base such as triethylamine or potassium carbonate in a solvent such as N, N-dimethylformamide or toluene.
- a base such as triethylamine or potassium carbonate
- a solvent such as N, N-dimethylformamide or toluene.
- the compound of the general formula (VII) can be obtained by reacting at a temperature of from 11 ° C to the reflux temperature of the solvent in the absence or in the absence.
- Step 4 the compound of the general formula (VII) is reduced by a suitable method such as platinum, A catalytic reduction method using a metal catalyst such as nickel nickel or palladium carbon, a reduction method using nickel chloride and sodium borohydride, a reduction method using iron powder and hydrochloric acid, etc.
- a suitable method such as platinum, A catalytic reduction method using a metal catalyst such as nickel nickel or palladium carbon, a reduction method using nickel chloride and sodium borohydride, a reduction method using iron powder and hydrochloric acid, etc.
- the compound of (VIII) can be obtained.
- the reduction reaction can be carried out in a solvent such as water, methanol, ethanol, tetrahydrofuran or a mixed solvent thereof at a temperature between 0 and the reflux temperature of the solvent.
- a solvent such as water, methanol, ethanol, tetrahydrofuran or a mixed solvent thereof at a temperature between 0 and the reflux temperature of the solvent.
- Step 5 the compound of the general formula (VIII) is combined with the following general formula (XI), (XII) or (XIII)
- R represents a lower alkyl group
- X represents a halogen atom
- ⁇ Has the same meaning as!? ⁇ (Excluding the hydroxyl group.)
- Step 6 a compound of the general formula (VIII) and a compound of the following general formula (XIV)
- Step 7 the compound of the above general formula (VIII) and the following general formula (XV) R '' COOH (XV)
- the compound of formula (1) is reacted at 0 ° C to 200 ° C in the presence or absence of an acid catalyst such as hydrochloric acid or sulfuric acid, in the presence or absence of a solvent such as N, N-dimethylformamide or toluene.
- an acid catalyst such as hydrochloric acid or sulfuric acid
- a solvent such as N, N-dimethylformamide or toluene.
- the compound of the general formula (X) may be treated, if necessary, with a protecting group such as an alkanoyl group, which binds a nitrogen atom which is not bonded to the adjacent (CH 2 ) m group of the saturated nitrogen-containing heterocyclic group represented by R 3.
- a suitable chlorinating agent for example, phosphorus oxychloride, thionyl chloride, phosgene, oxalyl chloride, phosphorus pentachloride, etc. in the presence or absence of a solvent such as toluene at 0 °.
- the compound is reacted at a temperature between C and 200 ° C., and if necessary, deprotected by a conventional method to obtain a compound of the general formula (IX) in which R 6 is a chlorine atom.
- the compound of the general formula (VIII) is combined with triphosgene in the presence of a base such as triethylamine or potassium carbonate in the presence of 1,2-dichloromethane, 1,4-dioxane, tetrahydrofuran,
- a base such as triethylamine or potassium carbonate
- 1,2-dichloromethane, 1,4-dioxane, tetrahydrofuran By reacting in a solvent such as N, N-dimethylformamide or toluene between 0 ° C and the reflux temperature of the solvent, the compound represented by the general formula (XVI)
- aryl substituted with a methylthio group as R 1 ′ is used.
- the compound of the general formula (IX) having a phenyl group as a substituent is optionally substituted with a nitrogen atom which is not bonded to the adjacent (CH 2 ) m group of the saturated nitrogen-containing heterocyclic group represented by R 3 by a conventional method.
- an appropriate oxidation reaction is carried out, and if necessary, deprotection is carried out by a conventional method.
- Z represents an aromatic ring
- a represents an integer of 1 or 2
- R 3 , R 6 , m, and A ⁇ have the same meanings as described above.
- the oxidation reaction can be performed by various methods according to the target substance. That is, when a represents an integer of 1, for example, using an oxidizing agent such as chromic acid, hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, or potassium periodate, In the case of representing an integer, for example, using oxidizing agents such as chromic acid, hydrogen peroxide, m-chloroperbenzoic acid, osmium tetroxide, ruthenium tetroxide, tetrahydrofuran, 1,4-dioxane It can be produced by reacting in 0, 1,2-dichloroethane, methanol, acetone or water, or a mixed solvent thereof between 0 ° C and the reflux temperature of the solvent.
- an oxidizing agent such as chromic acid, hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, or potassium periodate
- oxidizing agents such as chromic acid, hydrogen peroxide
- a compound of the general formula (I) in which R 2 is a chlorine atom is prepared by using water and an appropriate acid or base in a solvent at 0 ° C. to the reflux temperature of the solvent.
- Suitable acids include, for example, organic acids such as formic acid, acetic acid, and trifluoroacetic acid, and mineral acids such as hydrochloric acid, sulfuric acid, and hydrobromic acid.
- Suitable bases include, for example, sodium hydroxide and the like. Al force of metal or magnesium or calcium Examples include hydroxides, carbonates or bicarbonates of lithium earth metals.
- the solvent examples include alcohols such as methanol, ethanol, and n-propanol, N, N-dimethylformamide, , 4-dioxane, tetrahydrofuran and the like, or their hydrated solvents.
- the compound of the general formula (I) in which R 2 is a chlorine atom and R 1 is R 11 , or the general formula (I) in which R 2 is a hydroxyl group and R 1 is R ′′ A compound obtained by reacting the compound of formula (1) with trifluoromethanesulfonic anhydride, methyl sulfonyl chloride or p-toluene sulfonyl chloride, and a metal halide (eg, lithium fluoride, sodium fluoride, lithium fluoride) , Potassium bromide, sodium bromide, potassium iodide, sodium iodide, etc.) in an aprotic polar solvent such as dimethyl sulfoxide, N, N-dimethylformamide or acetonitrile.
- a metal halide eg, lithium fluoride, sodium fluoride, lithium fluoride
- aprotic polar solvent such as dimethyl sulfoxide, N, N-dimethylform
- R 2 is a fluorine atom, bromine atom or iodine atom, 1 1 to give a compound of 1 1 'Dearu over general formula (I).
- R 3 are adjacent (CH 2) on the nitrogen atom not bound to the m group, Arukanoiru group, an alkoxycarbonyl group, Baie Njiru group, Torifuruo
- a compound that is a saturated nitrogen-containing heterocyclic group having a protective group such as a methyl group is deprotected using an acid or alkali or a catalytic reduction reaction using a metal catalyst, depending on the type of the nitrogen-protecting group.
- a compound can be obtained in which R 3 is a saturated nitrogen-containing heterocyclic group in which the nitrogen atom not bonded to the adjacent (CH 2 ) m group is deprotected.
- the deprotection reaction using an acid or an alkali can be carried out by using a suitable acid or base and reacting in a solvent in the presence or absence of a cationic benzene such as anisol or thioanisole.
- a cationic benzene such as anisol or thioanisole.
- the solvent used include ethyl acetate, methylene chloride, 1,2-dichloroethane, 1,4-dioxane, methanol, ethanol, n-propanol, N, N-dimethylformamide, and tetrahydrochloride.
- examples thereof include drofuran or water, or a mixed solvent thereof.
- Examples of the acid used include hydrochloric acid, ethyl acetate solution of hydrogen chloride, ethanol solution of hydrogen chloride, sulfuric acid, hydrobromic acid, trifluoroacetic acid, methanesulfonic acid, and
- Examples of the base include toluenesulfonic acid, formic acid, and acetic acid.
- Examples of the base include hydroxides, carbonates, and hydrogencarbonates of alkaline metals such as sodium hydroxide and alkaline earth metals such as magnesium and calcium.
- the reaction can be carried out at a temperature between 0 ° C. and the reflux temperature of the solvent.
- the catalytic reduction reaction is carried out using an appropriate metal catalyst such as platinum, palladium carbon, Raney nickel, Pearlman's reagent, etc.
- reaction in water, alcohols such as methanol, ethanol, n-propanol, acetic acid, or a mixed solvent thereof.
- the reaction can be carried out in the presence or absence of an acid such as hydrochloric acid between room temperature and the reflux temperature of the solvent at a pressure from normal pressure to 200 kg / cm 2 .
- a compound of the general formula (I) wherein R 2 is a chlorine atom and a phenol derivative which may have a substituent are synthesized by using sodium hydroxide, potassium hydroxide or the like.
- R 2 is substituted.
- the compound of the general formula (I) in which R 2 is a chlorine atom is converted to an amine derivative or a substituent having one or two substituents.
- the compound of the general formula (I) in which R 2 obtained by the ninth synthesis method is a benzylamino group, a dibenzylamino group or a p-methoxybenzylamino group, by catalytic reduction using a suitable metal catalyst, or, R 2 is p - a compound which is a main butoxy benzyl ⁇ amino group, by a deprotection reaction child with an acid, in which it R 2 is amino groups
- R 2 is p - a compound which is a main butoxy benzyl ⁇ amino group
- the catalytic reduction reaction is carried out at room temperature to the reflux temperature of the solvent in an alcohol such as methanol or ethanol or water, or a mixed solvent thereof, under normal pressure or under pressure, under conditions of hydrochloric acid, acetic acid, formic acid, etc.
- an alcohol such as methanol or ethanol or water, or a mixed solvent thereof
- hydrochloric acid such as acetic acid, formic acid, etc.
- a metal catalyst such as palladium carbon, Pearlman's reagent
- the deprotection reaction using an acid is carried out in a solvent such as an alcohol such as methanol or ethanol, a solvent such as methylene chloride, 1,2-dichloroethane, 1,4-dioxane, tetrahydrofuran, toluene, N, N-dimethylformamide.
- a solvent such as an alcohol such as methanol or ethanol
- a solvent such as methylene chloride, 1,2-dichloroethane, 1,4-dioxane, tetrahydrofuran, toluene, N, N-dimethylformamide.
- an acid such as hydrochloric acid, sulfuric acid, trifluoroacetic acid, or trifluoromethanesulfonic acid in the presence or absence of a cation force venger such as anisol or thioanisole, and the reflux temperature of the solvent from 0 ° C Can be done between
- a compound in which R 3 is a saturated nitrogen-containing heterocyclic group having an ethylenedioxy group as a substituent in the general formula (I) is prepared by converting hydrochloric acid, hydrogen chloride, ethyl acetate solution, chloride Hydrogen ethanol solution, sulfuric acid, hydrobromic acid, trifluoroacetic acid, P-toluenesulfonic acid, formic acid, acetic acid, and other acids are used to prepare ethyl acetate, methylene chloride, 1,4-dioxane, tetrahydrofuran, methanol, Ethanol, n- By reacting at 0 ° C to 200 ° C in the presence or absence of a solvent such as propanol, N, N-dimethylformamide or a water-containing solvent thereof, R in the general formula (I) Compound 3 is a saturated nitrogen-containing heterocyclic group having an oxo group as
- R 7 represents a hydrogen atom or an alkyl group.
- the compound of formula (I) is reacted with methanol, ethanol, and n-amine in the presence or absence of bases such as triethylamine, diisopropylethylamine, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and sodium acetate.
- bases such as triethylamine, diisopropylethylamine, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and sodium acetate.
- a compound of the general formula (I) in which R 2 is a chlorine atom is converted to a compound such as platinum, palladium carbon or the like in the presence or absence of an acid such as hydrochloric acid or acetic acid.
- a compound of the general formula (I) wherein R 2 is a hydrogen atom by catalytic reduction in an alcoholic solvent such as methanol or ethanol or an aqueous solvent thereof at room temperature to the reflux temperature of the solvent with a metal catalyst under atmospheric pressure. can be obtained.
- R 3 is a saturated nitrogen-containing heterocyclic group having no protecting group at a nitrogen atom which is not bonded to an adjacent (CH 2 ) m group.
- R 3 is a saturated nitrogen-containing heterocyclic group having an appropriate substituent at a nitrogen atom not bonded to the adjacent (CH 2 ) m group.
- the reaction was N, N-dimethylformamide, methylene chloride, tetrahydrofuran, Triethylamine, potassium carbonate, etc. in the presence or absence of solvents such as toluene, pyridine, nitrobenzene, 1,2-dichloroethane, 1,4-dioxane, methanol, ethanol, n-propanol or water, or a mixed solvent thereof
- solvents such as toluene, pyridine, nitrobenzene, 1,2-dichloroethane, 1,4-dioxane, methanol, ethanol, n-propanol or water, or a mixed solvent thereof
- the reaction can be carried out at 0 ° C to 200 ° C in the presence or absence of a base.
- Suitable reagents include, for example, alkyl halides, triphenylmethyl chloride, benzyl chloride, benzhydryl chloride, formic acid 'formalin mixture, acetyl chloride, acetic anhydride, trifluoroacetic anhydride, benzoyl chloride, benzyl carbonate, Ethyl chlorocarbonate, ditert-butyl dicarbonate, sodium cyanate, alkyl isocyanate, sodium thiocyanate, alkyl thiocyanate, 1H-vinylazo 1-carboxamidine, methanesulfonyl chloride, p-methyl chloride Examples include toluenesulfonyl, P-fluorobenzenesulfonyl chloride, urethane, alkyl urethane, thiourethane, and alkylthiourethane.
- R 3 is a saturated nitrogen-containing heterocyclic compound having an alkyl group or a benzyl group as a substituent on a nitrogen atom which is not bonded to an adjacent (CH 2 ) m group.
- a compound that is a cyclic group and an alkyl chlorocarbonate or benzyl chlorocarbonate are mixed in the presence or absence of a solvent such as methylene chloride or toluene, in the presence or absence of a base such as triethylamine or carbonated lime.
- R 3 in general formula (I) is not bonded to the adjacent (CH 2 ) m group.
- a compound which is a saturated nitrogen-containing heterocyclic group having a carbonyl group as a substituent can be obtained.
- the compounds represented by the general formulas (II0 to (VIII)) used as starting materials and intermediates in the production method of the compound of the present invention are partially known compounds, for example, Journal of Medicinal Chemistry, Vol. 18, page 726. Vol. 33, p. 1880 (1990); Vol. 40, p. 1779 (1997), International Patent Publication No. 97/20820, European Patent Publication No. 223124 (1987). Etc., and can be produced according to the methods described therein.In addition, for some novel compounds, the production methods are described as reference examples.
- compositions containing the novel 1 H-imidazopyridine derivative represented by the above general formula (I) or (II) or a salt thereof as an active ingredient produced in this manner are usually capsules, tablets, and fine granules.
- Oral preparations such as granules, powders, powders, syrups and dry syrups, or parenteral injections such as injections, suppositories, eye drops, eye ointments, ear drops, nasal drops, dermatological agents, inhalants, etc. It is administered as a formulation.
- These preparations can be manufactured by a conventional method by adding pharmacologically and pharmaceutically acceptable additives.
- excipients lactose, D-mannitol, corn starch, crystalline cellulose, etc.
- disintegrants carboxymethylcellulose, etc.
- binders Hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinylpyrrolidone, etc.
- lubricants magnesium stearate, talc, etc.
- coating agents hydroxypropylmethylcellulose, sucrose, titanium oxide, etc.
- base materials polyethylene
- pharmaceutical ingredients such as glycols, hard fats, etc.
- aqueous or solubilizers or solubilizers that can constitute a dissolvable dosage form when used (distilled water for injection).
- Physiological saline, propylene glycol, etc. pH regulator (inorganic Is an organic acid or base), isotonic agents (salts, glucose, glycerin, etc.), stabilizers, etc.
- ophthalmic ointments and dermatological agents are ointments, creams, Appropriate formulation components (white petrolatum, macrogol, glycerin, cotton cloth, etc.) are used as patches.
- the dose of this compound to treated patients depends on the patient's symptoms, but is usually about 0.1 to 100 mg for oral administration and 0.0 for parenteral administration as a daily dose for adults. About 1 to 500 mg can be administered once or several times a day. However, it is desirable to appropriately increase or decrease the dose according to the purpose of treatment or prevention, the site and type of the disease, the age and symptoms of the patient.
- Methanesulfonic acid (N-triphenylmethyl-4-piperidyl) methyl Under ice-cooling, 84.0 g of N-triphenylmethyl-4-piperidinemethanol and 36.2 ml of triethylamine were added to a 420 ml solution of anhydrous tetrahydrofuran in 420 ml of anhydrous methanesulfonyl chloride. 3 ml was added dropwise, and the mixture was stirred at room temperature for 5.5 hours. Water was added to the reaction mixture and extracted with getyl ether.
- the extract was washed successively with water and saturated saline, and then dehydrated.
- the solvent was distilled off, a mixed solution of isopropanol and methanol was added, and the precipitated crystals were collected by filtration and washed with methanol. 90.4 g of colorless crystals were obtained. Recrystallization from a mixture of methylene chloride and methanol gave colorless prisms having a melting point of 129.5 to 134 ° C.
- Recrystallization solvent methanol-rugetyl ether
- the solid obtained by evaporating the solvent was washed with n-heptane to obtain 54.4 g of colorless crystals.
- 22.9 g of sodium azide and 220 ml of ⁇ , ⁇ -dimethylformamide were added to the obtained crystals, and the mixture was stirred at 70 C for 4 hours.
- insolubles were removed by filtration, and the filtrate was concentrated, and water was added to the obtained residue, followed by extraction with ethyl acetate.
- the extract was washed successively with water and saturated saline and then dehydrated, and the solvent was distilled off to obtain 43.2 g of a yellow liquid.
- N-triphenylmethyl-4-piperidineacetic acid 23.6 g, potassium carbonate 16.
- a suspension of 9 g and 5.0 ml of anhydrous N, N-dimethylformamide in 5.0 ml of suspension was stirred at 90 ° C for 5 hours. After cooling, water and ethyl acetate were added to the reaction mixture, and the precipitated crystals were collected by filtration and washed with water to obtain 20.6 g of colorless crystals. Recrystallization from a mixed solution of methanol and tetrahydrofuran gave colorless crystals having a melting point of 165 to 166 ° C.
- lithium aluminum hydride (4.77 g) was added to a suspension of 4.70 g of anhydrous tetrahydrofuran (2 50 ml). A solution of 7 g of anhydrous tetrahydrofuran in 250 ml was added dropwise, and the mixture was stirred at room temperature for 4 hours. Under ice-cooling, a mixture of tetrahydrofuran and a 10% aqueous sodium hydroxide solution was added dropwise to the reaction mixture. After filtering off the insolubles, the residue was washed with tetrahydrofuran, and the combined filtrate and washings were concentrated to obtain 48.1 g of a colorless liquid.
- the obtained brown crystals were purified by silica gel column chromatography using ethyl acetate-n-hexane (1: 3) as an eluting solvent to obtain 10.6 g of pale brown crystals. Recrystallization from ⁇ -hexane gave pale brown crystals with a melting point of 96-97 ° C.
- the extract is washed successively with water and saturated saline, and after dehydration, the solvent is removed. Distilled off. A solution of 3.03 g of the obtained pale yellow solid and 0.30 g of p-toluenesulfonic acid monohydrate in 100 ml of toluene was refluxed for 20 hours. After the reaction, the solvent was distilled off, and methanol and acetone were added to the residue, and the precipitated crystals were collected by filtration to obtain 1.79 g of colorless crystals.
- the extract was washed successively with a saturated aqueous solution of sodium bicarbonate and a saturated saline solution and then dehydrated, and the solvent was distilled off to obtain a reddish brown liquid.
- the obtained liquid was purified by silica gel column chromatography using ethyl acetate-n-heptane (1: 1) as an eluting solvent, and washed with diisopropyl ether to obtain 0.55 g of a colorless solid. Recrystallization from diisopropyl ether gave colorless crystals having a melting point of 146-16.5 ° C.
- the resulting brown liquid was purified by silica gel column chromatography using ethyl acetate as a dissolving solvent to obtain 3.59 g of a colorless solid. Recrystallization from a mixture of ethyl acetate and n-hexane gave colorless crystals having a melting point of 130.5-132.5 ° C.
- the obtained residue was purified by alumina column chromatography using methylene chloride-methanol chloride (100: 1, 20: 1) as an elution solvent, and washed with diisopropyl ether to obtain 1.88 g of colorless crystals. Recrystallization from ethyl acetate gave colorless crystals having a melting point of 193 193.5 C.
- the obtained liquid was purified by alumina column chromatography using ethyl acetate-n-heptane (1: 1) as a solvent to obtain 0.32 g of colorless crystals. Recrystallization from isopropanol gave colorless needles mp 163-165 ° C.
- the aqueous layer was adjusted to pH 11 with a 10% aqueous sodium hydroxide solution, and extracted from a mixed solution of 1,2-dichloroethane and methanol.
- the extract was washed with saturated saline and then dehydrated, and the solvent was distilled off to obtain 1.74 g of a colorless liquid.
- a part of the colorless liquid was converted into a hydrochloride by a conventional method, and recrystallized from methanol to obtain colorless crystals having a melting point of 257 to 265 ° C (decomposition).
- a fumarate was formed by a conventional method, and recrystallized from methanol to obtain colorless crystals having a melting point of 185.5 to 186.5 ° C (decomposition).
- the obtained liquid was dissolved in tetrahydrofuran, filtered using silica gel, and the filtrate was concentrated to obtain 0.87 g of a colorless solid. It was converted into a hydrochloride by a conventional method, and recrystallized from a mixture of methanol and ethyl acetate to obtain colorless crystals having a melting point of 144 to 158 ° C.
- the obtained colorless liquid was solidified with ethyl acetate and washed with diethyl ether to obtain 0.80 g of colorless crystals. Recrystallization from a mixture of methylene chloride and ethyl acetate gave colorless crystals having a melting point of 173.5-176 ° C.
- Example 201 Experimental value C, 60.79; H, 6.66; N, 21.97 According to the method of Example 200, the compound of Example 201 was obtained ( Example 201).
- PBMCs peripheral blood mononuclear cells
- LeucoPREP TM Becton Dickinson
- 2 mM L-glutamine Life Technologies
- 2.5 U / ml penicillin 1-2,5 ⁇ G / ml streptomycin Tomaishin contain a solution (Life Technologies)
- 10% fetal calf serum-(Intergen Company) was added RPMI-1640 medium (Nissui Pharmaceutical Co., Ltd.), a cell density 1 x 10 6 cells / ml
- the culture was performed as follows.
- test compound was dissolved in sterile ultrapure water, dimethyl sulfoxide, or 0.1 N hydrochloric acid to a concentration of 20 M, and serially diluted with physiological saline before use. Compounds were tested in a concentration range of 10- 1 () M ⁇ l 0- 5 M .
- a 96-well (flat bottom) MicroTest III TM tissue culture plate (Becton Dickinson) containing 180 ⁇ 1 of PBMC in the above medium was added with 1 ⁇ g / ml lipopolysaccharide (LPS) to a plate for cell culture. was added. Thirty minutes later, an additional 10 ⁇ 1 of the solution or solvent of the test compound was added to the gel, the plate was capped with a plastic lid, and incubated at 37% for 16 hours in a 5% carbon dioxide atmosphere.
- LPS lipopolysaccharide
- the enzymimnoassay method by the sandwich method was constructed to TNF-human IL-1? Was quantified.
- a 96-well microtiter plate was coated with diluted anti-cytoin antibody (primary antibody) and coated. ⁇ : After washing the cells, the culture supernatant was appropriately diluted and placed in a well for incubation. Thereafter, a secondary antibody to the cytokine and a tertiary antibody to the secondary antibody were sequentially added while interposing a washing step. After the final washing, a tetramethylbenzidine solution (DAKO) was added to each gel to start a color development reaction.
- DAKO tetramethylbenzidine solution
- Recombinant human TNF— (INTERGEN) were used as primary, secondary, and tertiary antibodies and standards for calibration curves, respectively.
- Monoclonal anti-human IL-1 (Cistron), polyclonal hidge anti-human IL-1 (Biogenesis), HRP-conjugated donkey anti-goat IgG (Chemicon International), Recombinant human IL-1? (R & D Systems) was used as the primary, secondary, tertiary antibody and standard for calibration curve, respectively.
- each test compound was determined by the amount of cytokine induced by treatment with LPS and the test compound, and the amount of cytokine induced by treatment with LPS alone. Expressed as a percentage (%) divided by
- the compound of the present invention exhibits an excellent production inhibitory effect on TNF and IL-1 and is extremely useful as an agent for preventing or treating diseases caused by these cytokines,
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Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
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EA200100230A EA200100230A1 (ru) | 1998-08-12 | 1999-08-12 | Производные 1h-имидазопиридина |
CA002339562A CA2339562A1 (en) | 1998-08-12 | 1999-08-12 | 1h-imidazopyridine derivatives |
EP99937053A EP1104764A4 (en) | 1998-08-12 | 1999-08-12 | 1H-IMIDAZOPYRIDINE DERIVATIVES |
AU51974/99A AU744388B2 (en) | 1998-08-12 | 1999-08-12 | 1H-imidazopyridine derivatives |
NZ509939A NZ509939A (en) | 1998-08-12 | 1999-08-12 | 1H-imidazopyridine derivatives useful as TNF or IL-1 inhibitors |
BR9914306-2A BR9914306A (pt) | 1998-08-12 | 1999-08-12 | Derivados do 1h-imidazopiridina |
IL14122699A IL141226A0 (en) | 1998-08-12 | 1999-08-12 | 1h-imidazopyridine derivatives |
PL99346155A PL346155A1 (en) | 1998-08-12 | 1999-08-12 | 1h-imidazopyridine derivatives |
HU0103406A HUP0103406A3 (en) | 1998-08-12 | 1999-08-12 | 1h-imidazopyridine derivatives and pharmaceutical compositions thereof |
US09/744,959 US6518265B1 (en) | 1998-08-12 | 1999-08-12 | 1H-imidazopyridine derivatives |
SK194-2001A SK1942001A3 (en) | 1998-08-12 | 1999-08-12 | 1h-imidazopyridine derivatives |
NO20010676A NO20010676L (no) | 1998-08-12 | 2001-02-09 | 1H-imidazopyridinderivater |
BG105271A BG105271A (en) | 1998-08-12 | 2001-02-19 | 1h-imidazopyridine derivatives |
HR20010144A HRP20010144A2 (en) | 1998-08-12 | 2001-02-28 | 1h-imidazopyridine derivatives |
HK02103246.4A HK1042295A1 (zh) | 1998-08-12 | 2002-04-30 | 1h-咪唑並吡啶衍生物 |
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JP24106298 | 1998-08-12 | ||
JP10/241062 | 1998-08-12 | ||
JP11/216125 | 1999-07-30 | ||
JP11216125A JP2000119271A (ja) | 1998-08-12 | 1999-07-30 | 1h―イミダゾピリジン誘導体 |
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EP (1) | EP1104764A4 (hu) |
JP (1) | JP2000119271A (hu) |
CN (1) | CN1323307A (hu) |
AU (1) | AU744388B2 (hu) |
BG (1) | BG105271A (hu) |
BR (1) | BR9914306A (hu) |
CA (1) | CA2339562A1 (hu) |
CZ (1) | CZ292544B6 (hu) |
EA (1) | EA200100230A1 (hu) |
HK (1) | HK1042295A1 (hu) |
HR (1) | HRP20010144A2 (hu) |
HU (1) | HUP0103406A3 (hu) |
IL (1) | IL141226A0 (hu) |
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NZ (1) | NZ509939A (hu) |
PL (1) | PL346155A1 (hu) |
SK (1) | SK1942001A3 (hu) |
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EP1599726A4 (en) | 2003-02-27 | 2009-07-22 | 3M Innovative Properties Co | SELECTIVE MODULATION OF TLR-MEDIATED BIOLOGICAL ACTIVITY |
CA2517528A1 (en) | 2003-03-04 | 2004-09-16 | 3M Innovative Properties Company | Prophylactic treatment of uv-induced epidermal neoplasia |
MXPA05009488A (es) * | 2003-03-07 | 2005-12-14 | 3M Innovative Properties Co | 1-amino 1h-imidazoquinolinas. |
US7163947B2 (en) | 2003-03-07 | 2007-01-16 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
EP1608282A4 (en) * | 2003-03-13 | 2010-12-08 | 3M Innovative Properties Co | METHODS OF DIAGNOSING SKIN LESIONS |
BRPI0408476A (pt) | 2003-03-13 | 2006-04-04 | 3M Innovative Properties Co | métodos para melhorar a qualidade da pele |
US7179253B2 (en) | 2003-03-13 | 2007-02-20 | 3M Innovative Properties Company | Method of tattoo removal |
US20040192585A1 (en) | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
JP2007500210A (ja) * | 2003-04-10 | 2007-01-11 | スリーエム イノベイティブ プロパティズ カンパニー | 金属含有微粒子担体材料を使用した免疫反応調節物質化合物の送達 |
US20040265351A1 (en) * | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
WO2004096144A2 (en) * | 2003-04-28 | 2004-11-11 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
AR044466A1 (es) * | 2003-06-06 | 2005-09-14 | 3M Innovative Properties Co | Proceso para la preparacion de imidazo [4,5-c] piridin-4-aminas |
WO2004110991A2 (en) * | 2003-06-06 | 2004-12-23 | 3M Innovative Properties Company | PROCESS FOR IMIDAZO[4,5-c]PYRIDIN-4-AMINES |
MXPA06001054A (es) * | 2003-07-31 | 2006-04-24 | 3M Innovative Properties Co | Composiciones bioactivas que comprenden triazinas. |
EP1651216A2 (en) * | 2003-08-05 | 2006-05-03 | 3M Innovative Properties Company | Infection prophylaxis using immune response modifier compounds |
AU2004266658A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
CA2535338C (en) * | 2003-08-14 | 2013-05-28 | 3M Innovative Properties Company | Substituted 1h-imidazo[4,5-c]pyridin-4-amines,1h-imidazo[4,5-c]quinolin -4-amines and 1h-imidazo[4,5-c]naphthyridin-4-amines as immune response modifiers |
WO2005020912A2 (en) * | 2003-08-25 | 2005-03-10 | 3M Innovative Properties Company | Delivery of immune response modifier compounds |
WO2005018574A2 (en) * | 2003-08-25 | 2005-03-03 | 3M Innovative Properties Company | Immunostimulatory combinations and treatments |
KR101106812B1 (ko) * | 2003-08-27 | 2012-01-19 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 아릴옥시 및 아릴알킬렌옥시 치환된 이미다조퀴놀린 |
AU2004268665A1 (en) * | 2003-09-02 | 2005-03-10 | 3M Innovative Properties Company | Methods related to the treatment of mucosal associated conditions |
EP1660026A4 (en) * | 2003-09-05 | 2008-07-16 | 3M Innovative Properties Co | TREATMENT FOR CD5 + B CELL LYMPHOMA |
SG149829A1 (en) | 2003-10-03 | 2009-02-27 | 3M Innovative Properties Co | Pyrazolopyridines and analogs thereof |
US20090075980A1 (en) * | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
JP2007509987A (ja) * | 2003-10-31 | 2007-04-19 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節剤化合物による好中球活性化 |
EP1685129A4 (en) | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
JP2007511535A (ja) | 2003-11-14 | 2007-05-10 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドロキシルアミン置換イミダゾ環化合物 |
KR20060117329A (ko) * | 2003-11-21 | 2006-11-16 | 노파르티스 아게 | 단백질 키나제 저해제로서의 1h-이미다조퀴놀린 유도체 |
CA2547085A1 (en) * | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
US20050226878A1 (en) * | 2003-12-02 | 2005-10-13 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
US8940755B2 (en) | 2003-12-02 | 2015-01-27 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
JP2007513170A (ja) * | 2003-12-04 | 2007-05-24 | スリーエム イノベイティブ プロパティズ カンパニー | スルホン置換イミダゾ環エーテル |
US8802853B2 (en) * | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
CA2552101A1 (en) * | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Piperazine, [1,4]diazepane, [1,4]diazocane, and [1,5]diazocane fused imidazo ring compounds |
JP2007517044A (ja) * | 2003-12-30 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | イミダゾキノリニル、イミダゾピリジニル、およびイミダゾナフチリジニルスルホンアミド |
WO2005067500A2 (en) * | 2003-12-30 | 2005-07-28 | 3M Innovative Properties Company | Enhancement of immune responses |
WO2005089317A2 (en) | 2004-03-15 | 2005-09-29 | 3M Innovative Properties Company | Immune response modifier formulations and methods |
WO2005094531A2 (en) * | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
WO2005110013A2 (en) * | 2004-04-09 | 2005-11-24 | 3M Innovative Properties Company | Methods, compositions, and preparations for delivery of immune response modifiers |
CN101426524A (zh) * | 2004-04-28 | 2009-05-06 | 3M创新有限公司 | 用于粘膜接种疫苗的组合物和方法 |
US20050267145A1 (en) * | 2004-05-28 | 2005-12-01 | Merrill Bryon A | Treatment for lung cancer |
PT1765310E (pt) | 2004-05-28 | 2016-03-01 | Oryxe | Uma mistura para entrega transdérmica de compostos de baixo e alto peso molecular |
WO2005123079A2 (en) * | 2004-06-14 | 2005-12-29 | 3M Innovative Properties Company | Urea substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
US8017779B2 (en) * | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
US7897609B2 (en) | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
US8026366B2 (en) * | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
JP5128940B2 (ja) * | 2004-06-18 | 2013-01-23 | スリーエム イノベイティブ プロパティズ カンパニー | 置換イミダゾキノリン、イミダゾピリジン、およびイミダゾナフチリジン |
US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
US20060045886A1 (en) * | 2004-08-27 | 2006-03-02 | Kedl Ross M | HIV immunostimulatory compositions |
CA2578975A1 (en) | 2004-09-02 | 2006-03-16 | 3M Innovative Properties Company | 2-amino 1h imidazo ring systems and methods |
EP1789042B1 (en) * | 2004-09-02 | 2012-05-02 | 3M Innovative Properties Company | 1-alkoxy 1h-imidazo ring systems and methods |
US20090270443A1 (en) * | 2004-09-02 | 2009-10-29 | Doris Stoermer | 1-amino imidazo-containing compounds and methods |
US20080193468A1 (en) * | 2004-09-08 | 2008-08-14 | Children's Medical Center Corporation | Method for Stimulating the Immune Response of Newborns |
WO2006042254A2 (en) * | 2004-10-08 | 2006-04-20 | 3M Innovative Properties Company | Adjuvant for dna vaccines |
EA200700244A1 (ru) * | 2004-12-27 | 2007-06-29 | Ю Эс Ви ЛИМИТЕД | СПОСОБ ПОЛУЧЕНИЯ 4-АМИНО-1-ИЗОБУТИЛ-1H-ИМИДАЗО-[4,5-c]ХИНОЛИНА (ИМИХИМОД) |
US8436176B2 (en) | 2004-12-30 | 2013-05-07 | Medicis Pharmaceutical Corporation | Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine |
US8461174B2 (en) * | 2004-12-30 | 2013-06-11 | 3M Innovative Properties Company | Treatment for cutaneous metastases |
JP2008526751A (ja) * | 2004-12-30 | 2008-07-24 | 武田薬品工業株式会社 | 1−(2−メチルプロピル)−1h−イミダゾ[4,5−c][1,5]ナフチリジン−4−アミンエタンスルホナート及び1−(2−メチルプロピル)−1h−イミダゾ[4,5−c][1,5]ナフチリジン−4−アミンメタンスルホナート |
US7943609B2 (en) * | 2004-12-30 | 2011-05-17 | 3M Innovative Proprerties Company | Chiral fused [1,2]imidazo[4,5-C] ring compounds |
WO2006083440A2 (en) | 2004-12-30 | 2006-08-10 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
JP2008530252A (ja) | 2005-02-09 | 2008-08-07 | コーリー ファーマシューティカル グループ,インコーポレイテッド | オキシムおよびヒドロキシルアミンで置換されたチアゾロ[4,5−c]環化合物ならびに方法 |
US20080318998A1 (en) * | 2005-02-09 | 2008-12-25 | Coley Pharmaceutical Group, Inc. | Alkyloxy Substituted Thiazoloquinolines and Thiazolonaphthyridines |
EP1845988A2 (en) * | 2005-02-11 | 2007-10-24 | 3M Innovative Properties Company | Substituted imidazoquinolines and imidazonaphthyridines |
EP1846405A2 (en) | 2005-02-11 | 2007-10-24 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted imidazo 4,5-c ring compounds and methods |
JP2008538203A (ja) | 2005-02-23 | 2008-10-16 | コーリー ファーマシューティカル グループ,インコーポレイテッド | インターフェロンの生合成を優先的に誘導する方法 |
EP1851224A2 (en) * | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
WO2006091567A2 (en) * | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
EP1851220A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
CN101175493A (zh) | 2005-03-14 | 2008-05-07 | 3M创新有限公司 | 治疗光化性角化病的方法 |
CA2602590A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
JP2008535832A (ja) | 2005-04-01 | 2008-09-04 | コーリー ファーマシューティカル グループ,インコーポレイテッド | ピラゾロピリジン−1,4−ジアミン、およびそのアナログ |
US20080193474A1 (en) * | 2005-04-25 | 2008-08-14 | Griesgraber George W | Immunostimulatory Compositions |
GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
WO2007003961A2 (en) * | 2005-06-30 | 2007-01-11 | Prosidion Limited | Gpcr agonists |
CA2621831A1 (en) | 2005-09-09 | 2007-03-15 | Coley Pharmaceutical Group, Inc. | Amide and carbamate derivatives of n-{2-[4-amino-2- (ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods |
ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
EP1948185A4 (en) * | 2005-11-10 | 2010-04-21 | Glaxosmithkline Llc | INHIBITORS OF AKT ACTIVITY |
JP2009515884A (ja) * | 2005-11-10 | 2009-04-16 | スミスクライン・ビーチャム・コーポレイション | Akt活性の阻害剤 |
LT2474545T (lt) | 2005-12-13 | 2017-02-27 | Incyte Holdings Corporation | Heteroarilu pakeisti pirolo[2,3-b]piridinai ir pirolo[2,3-b]pirimidinai kaip janus kinazės inhibitoriai |
ES2374455T3 (es) | 2006-02-17 | 2012-02-16 | Pfizer Limited | Derivados de 3-deazapurinza como moduladores de tlr7. |
US8951528B2 (en) * | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
US8329721B2 (en) * | 2006-03-15 | 2012-12-11 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1H-imidazonaphthyridines and methods |
US7906506B2 (en) | 2006-07-12 | 2011-03-15 | 3M Innovative Properties Company | Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods |
WO2008030511A2 (en) * | 2006-09-06 | 2008-03-13 | Coley Pharmaceuticial Group, Inc. | Substituted 3,4,6,7-tetrahydro-5h, 1,2a,4a,8-tetraazacyclopenta[cd]phenalenes |
US8436177B2 (en) | 2006-11-20 | 2013-05-07 | Novartis Ag | Salts and crystall forms of 2-methyl-2-[4-(3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-propionitrile |
US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
LT3070090T (lt) | 2007-06-13 | 2019-06-25 | Incyte Holdings Corporation | Janus kinazės inhibitoriaus (r)-3-(4-(7h-pirol[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)-3-ciklopentilpropannitrilo druskų panaudojimas |
GB0715428D0 (en) * | 2007-08-08 | 2007-09-19 | Imp Innovations Ltd | Compositions and uses thereof |
WO2009125809A1 (ja) * | 2008-04-11 | 2009-10-15 | 第一三共株式会社 | ピペリジン誘導体 |
WO2009125808A1 (ja) * | 2008-04-11 | 2009-10-15 | 第一三共株式会社 | アミノシクロヘキシル誘導体 |
JP5775070B2 (ja) | 2009-05-22 | 2015-09-09 | インサイト・コーポレイションIncyte Corporation | ヤヌスキナーゼ阻害剤としてのピラゾール−4−イル−ピロロ[2,3−d]ピリミジンおよびピロール−3−イル−ピロロ[2,3−d]ピリミジンのN−(ヘテロ)アリール−ピロリジン誘導体 |
MY161416A (en) | 2009-05-22 | 2017-04-14 | Incyte Holdings Corp | 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4yl)-1h-pyrazol-1-yl]octane-or heptane-nitrile as jak inhibitors |
US20110033515A1 (en) * | 2009-08-04 | 2011-02-10 | Rst Implanted Cell Technology | Tissue contacting material |
US9249145B2 (en) | 2009-09-01 | 2016-02-02 | Incyte Holdings Corporation | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
AR081315A1 (es) | 2010-03-10 | 2012-08-08 | Incyte Corp | Derivados heterociclicos de piperidin y pirimidin -4-il-azetidina, una forma cristalina de la sal del acido acetonitriladipico de un derivado pirimidinico, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades relacionadas con la inhibicion de jak-1, t |
ME02445B (me) | 2010-05-21 | 2016-09-20 | Incyte Holdings Corp | Topikalna formulacija za inhibiciju jak-a |
WO2012024284A1 (en) | 2010-08-17 | 2012-02-23 | 3M Innovative Properties Company | Lipidated immune response modifier compound compositions, formulations, and methods |
AR083933A1 (es) | 2010-11-19 | 2013-04-10 | Incyte Corp | Derivados de pirrolopiridina y pirrolopirimidina sustituidos con ciclobutilo como inhibidores de jak |
JP2014504286A (ja) * | 2010-12-06 | 2014-02-20 | ピラマル エンタープライジーズ リミテッド | 置換イミダゾキノリン誘導体 |
BR112013031039B1 (pt) | 2011-06-03 | 2020-04-28 | 3M Innovative Properties Co | compostos de hidrazino 1h-imidazoquinolina-4-aminas, conjugados feitos destes compostos, composição e composição farmacêutica compreendendo ditos compostos e conjugados, usos dos mesmos e método de fabricação do conjugado |
CN103582496B (zh) | 2011-06-03 | 2016-05-11 | 3M创新有限公司 | 具有聚乙二醇链段的异双官能连接基以及由其制成的免疫应答调节剂缀合物 |
PE20140832A1 (es) | 2011-06-20 | 2014-07-14 | Incyte Corp | Derivados de azetidinil fenil, piridil o pirazinil carboxamida como inhibidores de jak |
US20130023736A1 (en) | 2011-07-21 | 2013-01-24 | Stanley Dale Harpstead | Systems for drug delivery and monitoring |
TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為jak抑制劑之環己基氮雜環丁烷衍生物 |
UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
RU2628074C2 (ru) | 2011-09-30 | 2017-08-14 | Си энд Си РИСЕРЧ ЛЭБОРЕТРИЗ | ТРИЦИКЛИЧЕСКИЕ АЗОТСОДЕРЖАЩИЕ ПРОИЗВОДНЫЕ ИМИДАЗО[4,5-с]ПИРИДИНА, ОБЛАДАЮЩИЕ ИНГИБИРУЮЩЕЙ АКТИВНОСТЬЮ В ОТНОШЕНИИ РЕЦЕПТОРА ГИСТАМИНА 4 (hH4R) |
WO2013162828A1 (en) | 2012-04-27 | 2013-10-31 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Use of cpg oligonucleotides co-formulated with an antibiotic to accelarate wound healing |
US9193733B2 (en) | 2012-05-18 | 2015-11-24 | Incyte Holdings Corporation | Piperidinylcyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as JAK inhibitors |
SG11201503141TA (en) * | 2012-11-01 | 2015-06-29 | Incyte Corp | Tricyclic fused thiophene derivatives as jak inhibitors |
CA3178452A1 (en) | 2012-11-15 | 2014-05-22 | Incyte Holdings Corporation | Sustained-release dosage forms of ruxolitinib |
CN105025854A (zh) | 2013-01-07 | 2015-11-04 | 宾夕法尼亚大学董事会 | 治疗皮肤t细胞淋巴瘤的组合物和方法 |
LT3489239T (lt) | 2013-03-06 | 2022-03-10 | Incyte Holdings Corporation | Jak inhibitoriaus gamybos būdai ir tarpiniai junginiai |
WO2014201245A1 (en) | 2013-06-12 | 2014-12-18 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Tlr-9 agonist with tlr-7 and/or tlr-8 agonist for treating tumors |
MY195091A (en) | 2013-08-07 | 2023-01-10 | Incyte Corp | Sustained Release Dosage Forms for a JAK1 Inhibitor |
US9227969B2 (en) * | 2013-08-14 | 2016-01-05 | Novartis Ag | Compounds and compositions as inhibitors of MEK |
CN106687462A (zh) | 2014-04-30 | 2017-05-17 | 因赛特公司 | Jak1抑制剂的制备方法以及其新形式 |
WO2015171526A2 (en) * | 2014-05-05 | 2015-11-12 | Global Blood Therapeutics, Inc. | Tricyclic pyrazolopyridine compounds |
WO2015184305A1 (en) | 2014-05-30 | 2015-12-03 | Incyte Corporation | TREATMENT OF CHRONIC NEUTROPHILIC LEUKEMIA (CNL) AND ATYPICAL CHRONIC MYELOID LEUKEMIA (aCML) BY INHIBITORS OF JAK1 |
WO2016183371A1 (en) | 2015-05-13 | 2016-11-17 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Methods for the treatment or prevention of ischemic tissue damage |
WO2017044803A1 (en) | 2015-09-09 | 2017-03-16 | The United States Of America, As Represented By The Secretary Department Of Health And Human Service | Expression vector delivery system and use thereof for inducing an immune response |
KR20180053318A (ko) | 2015-09-17 | 2018-05-21 | 제이알엑스 바이오테크놀로지, 인코포레이티드 | 피부 수화 또는 보습을 향상시키기 위한 접근법 |
WO2017059280A1 (en) | 2015-10-02 | 2017-04-06 | The University Of North Carolina At Chapel Hill | Novel pan-tam inhibitors and mer/axl dual inhibitors |
WO2017147597A1 (en) | 2016-02-27 | 2017-08-31 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Peptide vaccines comprising self-assembling polymer nanoparticles |
USRE49834E1 (en) * | 2016-10-03 | 2024-02-13 | Hangzhou Highlightll Pharmaceutical Co., Ltd. | Jak1 selective inhibitors and uses thereof |
KR20190131116A (ko) | 2017-04-04 | 2019-11-25 | 아비디아 테크놀로지스, 인크. | 펩티드-기반 백신, 그의 제조 방법, 및 면역 반응을 유도하기 위한 그의 용도 |
US10596161B2 (en) | 2017-12-08 | 2020-03-24 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
WO2019123178A1 (en) | 2017-12-20 | 2019-06-27 | 3M Innovative Properties Company | Amide substitued imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
WO2019152374A1 (en) | 2018-01-30 | 2019-08-08 | Incyte Corporation | Processes for preparing (1 -(3-fluoro-2-(trifluoromethyl)isonicotinyl)piperidine-4-one) |
EP3759129A1 (en) | 2018-02-28 | 2021-01-06 | Pfizer Inc | Il-15 variants and uses thereof |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0145340A2 (en) * | 1983-11-18 | 1985-06-19 | Riker Laboratories, Inc. | 1H-Imidazo[4,5-c]quinolines and 1H-imidazo[4,5-c]quinolin-4-amines |
US4689338A (en) * | 1983-11-18 | 1987-08-25 | Riker Laboratories, Inc. | 1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use |
EP0459505A1 (en) * | 1990-06-01 | 1991-12-04 | Kyowa Hakko Kogyo Co., Ltd. | Imidazonaphthyridine derivatives |
US5352784A (en) * | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
US5389640A (en) * | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
JPH09208584A (ja) * | 1996-01-29 | 1997-08-12 | Terumo Corp | アミド誘導体、およびそれを含有する医薬製剤、および合成中間体 |
WO1998030562A1 (fr) * | 1997-01-09 | 1998-07-16 | Terumo Kabushiki Kaisha | Nouveaux derives d'amide et intermediaires utilises pour leur synthese |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US346905A (en) * | 1886-08-10 | Heney gulick | ||
EP0223124B1 (en) | 1985-11-06 | 1991-06-12 | Merck & Co. Inc. | Substituted aminosulfonyl 6-nitrobenzoic-esters or amides, processes for their preparation and pharmaceutical compositions containing them |
US4988815A (en) | 1989-10-26 | 1991-01-29 | Riker Laboratories, Inc. | 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines |
US5268376A (en) * | 1991-09-04 | 1993-12-07 | Minnesota Mining And Manufacturing Company | 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
JP3206078B2 (ja) | 1992-01-28 | 2001-09-04 | 株式会社ノーリツ | 燃焼機の機種セレクト装置 |
WO1997020820A1 (en) | 1995-12-01 | 1997-06-12 | Novartis Ag | Heteroaryl compounds |
-
1999
- 1999-07-30 JP JP11216125A patent/JP2000119271A/ja active Pending
- 1999-08-11 TW TW088113701A patent/TW533209B/zh active
- 1999-08-12 NZ NZ509939A patent/NZ509939A/xx unknown
- 1999-08-12 PL PL99346155A patent/PL346155A1/xx unknown
- 1999-08-12 CA CA002339562A patent/CA2339562A1/en not_active Abandoned
- 1999-08-12 EA EA200100230A patent/EA200100230A1/ru unknown
- 1999-08-12 EP EP99937053A patent/EP1104764A4/en not_active Withdrawn
- 1999-08-12 AU AU51974/99A patent/AU744388B2/en not_active Ceased
- 1999-08-12 US US09/744,959 patent/US6518265B1/en not_active Expired - Fee Related
- 1999-08-12 WO PCT/JP1999/004381 patent/WO2000009506A1/ja not_active Application Discontinuation
- 1999-08-12 BR BR9914306-2A patent/BR9914306A/pt not_active IP Right Cessation
- 1999-08-12 TR TR2001/00439T patent/TR200100439T2/xx unknown
- 1999-08-12 CN CN99812056A patent/CN1323307A/zh active Pending
- 1999-08-12 HU HU0103406A patent/HUP0103406A3/hu unknown
- 1999-08-12 IL IL14122699A patent/IL141226A0/xx unknown
- 1999-08-12 CZ CZ2001503A patent/CZ292544B6/cs not_active IP Right Cessation
- 1999-08-12 SK SK194-2001A patent/SK1942001A3/sk unknown
-
2001
- 2001-02-09 NO NO20010676A patent/NO20010676L/no unknown
- 2001-02-19 BG BG105271A patent/BG105271A/xx active Pending
- 2001-02-28 HR HR20010144A patent/HRP20010144A2/hr not_active Application Discontinuation
-
2002
- 2002-04-30 HK HK02103246.4A patent/HK1042295A1/zh unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0145340A2 (en) * | 1983-11-18 | 1985-06-19 | Riker Laboratories, Inc. | 1H-Imidazo[4,5-c]quinolines and 1H-imidazo[4,5-c]quinolin-4-amines |
US4689338A (en) * | 1983-11-18 | 1987-08-25 | Riker Laboratories, Inc. | 1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use |
EP0459505A1 (en) * | 1990-06-01 | 1991-12-04 | Kyowa Hakko Kogyo Co., Ltd. | Imidazonaphthyridine derivatives |
US5389640A (en) * | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
US5352784A (en) * | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
JPH09208584A (ja) * | 1996-01-29 | 1997-08-12 | Terumo Corp | アミド誘導体、およびそれを含有する医薬製剤、および合成中間体 |
WO1998030562A1 (fr) * | 1997-01-09 | 1998-07-16 | Terumo Kabushiki Kaisha | Nouveaux derives d'amide et intermediaires utilises pour leur synthese |
Non-Patent Citations (2)
Title |
---|
J. INTERFERON RES., vol. 14, 1994, pages 81 - 85, XP002928463 * |
J. MED. CHEM., vol. 11, no. 1, 1968, pages 87 - 92, XP002928464 * |
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Also Published As
Publication number | Publication date |
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JP2000119271A (ja) | 2000-04-25 |
EA200100230A1 (ru) | 2001-10-22 |
AU744388B2 (en) | 2002-02-21 |
AU5197499A (en) | 2000-03-06 |
HUP0103406A3 (en) | 2002-11-28 |
TR200100439T2 (tr) | 2001-05-21 |
CA2339562A1 (en) | 2000-02-24 |
CZ2001503A3 (cs) | 2001-11-14 |
EP1104764A4 (en) | 2003-01-15 |
CN1323307A (zh) | 2001-11-21 |
HK1042295A1 (zh) | 2002-08-09 |
BR9914306A (pt) | 2002-05-21 |
HRP20010144A2 (en) | 2002-04-30 |
US6518265B1 (en) | 2003-02-11 |
IL141226A0 (en) | 2002-03-10 |
NZ509939A (en) | 2002-08-28 |
CZ292544B6 (cs) | 2003-10-15 |
TW533209B (en) | 2003-05-21 |
NO20010676D0 (no) | 2001-02-09 |
PL346155A1 (en) | 2002-01-28 |
BG105271A (en) | 2001-11-30 |
NO20010676L (no) | 2001-04-10 |
HUP0103406A2 (hu) | 2002-02-28 |
SK1942001A3 (en) | 2001-12-03 |
EP1104764A1 (en) | 2001-06-06 |
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